The cultural prestige accorded to Shakespeare's great roles has made them high watermarks for ‘great acting’ in general. They are therefore also uniquely capable of channelling a performer's sense of his own failure. The 1987 film Withnail & I famously ends with its title character, an out‐of‐work actor and self‐destructive alcoholic, delivering Hamlet's “What a piece of work is a man” to an audience of unresponsive wolves. And in 2014's The Trip to Italy, Steve Coogan plays a fictionalised version of himself: a comedian who fears he will never be remembered as a serious artist. On a visit to Pompeii, Coogan's delivery of Hamlet's speech to Yorick's skull similarly becomes a way of channelling the series's wider reflections on fame, mortality, and the value of the actor's art. Drawing on Marvin Carlson's argument that the role of Hamlet is unusually densely ghosted by its previous occupants, this article will explore how these two contemporary depictions of struggling performers evoke the received idea of the great Shakespearean role as the pinnacle of the actor's art to respond to the dilemma of how to cope with creative failure.